1 of 23
Following a holiday vacation in snowy Colorado, the Oscar winner was spotted stepping off a private jet in Los Angeles with the 20-year-old model. DiCaprio was first linked with Morrone in mid-December 2017 when he was spotted leaving her house. The model and actress joined the festivities in Colorado along with DiCaprio’s close friend Tobey Maguire and his two kids — Otis Tobias, 8, and Ruby Sweetheart, 11. "They are family friends and the two families are very close," a friend of DiCaprio and Morrone told PEOPLE.
2 of 23
In September 2017, DiCaprio was spotted spending some quality time with the German model at New York City's MoMA PS1. They continued their outing with a dinner date at Hillstone restaurant, according to Page Six. Although the actor's rep says "they're not dating," Rae was spotted among a group of revelers soaking up the sun on a yacht in St. Tropez with DiCaprio and his pal Tobey Maguire at the end of May.
3 of 23
DiCaprio and Agdal dated for a year after first being spotted at a New York City club in May 2016. Following their split, a source close to the actor told PEOPLE that he just wasn’t ready to take the next step. "Leo thought Nina was a super cool girl," said the source. "It almost seemed different this time because he was way more affectionate and public with her than he normally is, but his friends knew it wouldn't last."
The source added, "He's not ready to settle down and just isn't in the mindset to get married or have kids."
4 of 23
After a long day of movie premieres and exclusive events at the Cannes Film Festival in May 2016, the actor decided to let off some steam as he partied the night away at Gotha Club with the Victoria's Secret model. At one point, Fowler wrapped her arm around DiCaprio, pulling him closer to her, while they danced together.
5 of 23
Right before leaving for Cannes, DiCaprio took advantage of the beautiful spring weather in May 2016 by going on a bike ride around N.Y.C. with the Polish model. The night before their bike ride, the pair went to dinner together and attended a birthday celebration at N.Y.C. nightclub Marquee, where they appeared "couple-y." An eyewitness told Page Six the pair kept close the whole night: "They were dancing. Leo was dancing with her in his arms and canoodling. They were doing their thing, bumping and grinding."
6 of 23
In April 2016, the actor was spotted getting cozy with the model when they stepped out to grab dinner in New York City alongside DiCaprio's close friend Lukas Haas and another blonde. "She was very attached to Leo," a source told PEOPLE of Horner. "She was definitely with him, she was holding on to his arm. They were affectionate." Despite the evident PDA, the model addressed romance rumors in a series of tweets that have since been deleted. "You can't have a friend in the industry without people assuming it's more than that it's a joke," she wrote. In a second tweet, she assured fans that she did not go home with DiCaprio. "FYI we all went our separate ways home, as friends do."
7 of 23
DiCaprio and the Sports Illustrated model began dating in the summer of 2015, and were spotted riding around New York City on Citi bikes that June. The couple was never shy about showing some PDA – they were often seen kissing and holding hands while on outings. After a few months together, the actor and model called it quits, with a source telling PEOPLE that scheduling conflicts led to their breakup. "They are very friendly and it's super amicable," an insider close to the pair shared in January 2016. "They are both so busy and he's got a big movie coming out and she's one of the biggest supermodels in the world. There is no other person in the picture."
8 of 23
Cleary, who was a contestant on America's Next Top Model, was photographed in Cannes in May 2014 with DiCaprio. A spokesperson for the model, who was separated from but still legally married to husband Andrew Stern at the time, told PEOPLE that "any rumors of any kind of extra-marital relationship are entirely fabricated and completely false," adding that Cleary's interaction with the Oscar winner "was fully for the purpose of potential collaboration for environmental and animal welfare issues."
9 of 23
Photographers spotted DiCaprio entertaining the Romanian model during his stay in Australia for The Great Gatsby in 2011. Reports said the rumored relationship lasted a few dinners before fizzling out.
10 of 23
DiCaprio and the Victoria's Secret model dated in 2013, making headlines after they were first spotted taking photos together while walking the grounds and gardens of France's Chateau de Versailles together. The pair initially connected at the Cannes Film Festival, where DiCaprio opened The Great Gatsby that year. But the duo seem to have recently reconnected: DiCaprio and Garrn were seen holding hands while leaving a New York City nightclub in September 2017.
11 of 23
Back in 2015, rumors circulated that the singer and actor were casually dating. A source told PEOPLE that although Rihanna and DiCaprio didn't act like a couple during the "Wild Thoughts" crooner's 27th birthday festivities, they did share a few flirtatious moments. "They weren't couple-y but they would flirt and dance so definitely a little magic there," said the onlooker. "They were definitely flirty and dancing, but not over the top."
12 of 23
After dating for nearly a year in 2011, the couple had an amicable spilt, citing the actor's demanding movie projects as the main factor. Despite splitting up, Heatherton and DiCaprio remain friendly, with the model calling the actor "a wonderful person" and "a friend of mine" in a 2015 interview.
13 of 23
Lively and DiCaprio romped it up around Europe in 2011 and dated for a few months — while the actress was shooting Gossip Girl during a brief time when the show was set in L.A. "When I think about shooting the L.A. episodes, Blake was dating [DiCaprio] at the time, and she had this thing where she had a doll that she took photos of that she sent to Leo," Gossip Girl executive producer Joshua Safran told Vanity Fair in 2017. They actors broke up later that year and the actress then started dating current hubby Ryan Reynolds.
14 of 23
Israeli model Refaeli started out as DiCaprio's stunning 20-year-old fling, but evolved into a serious relationship, which began in 2005 and officially came to an end in 2011. Many DiCaprio trackers thought the pair would settle down, especially after reconciling after a six-month break in 2010, but the couple did not reunite. Refaeli is now married to Adi Ezra with one daughter and another child on the way.
15 of 23
Before she was Adam Levine's ex, the Russian model (also known as Anne V. in the industry) was connected to DiCaprio in 2009. Some say that she and the actor had a brief romance while DiCaprio was on a break from his relationship with Refaeli.
16 of 23
She may be happily married to Super Bowl champ Tom Brady — with whom she shares two kids — but from 2000 to 2005, the supermodel was in a serious relationship with the actor. The couple went through several on-again, off-again moments before officially calling it quits almost six years after first linking up. "We were very young, and we grew together in a lot of ways," Bündchen said in a 2009 interview with Vanity Fair. "We were just not meant to be boyfriend and girlfriend, but I respect him enormously, and I wish him nothing but the best."
17 of 23
DiCaprio and Herzigova were said to have a one month relationship in 1998, but never confirmed the tryst. Perhaps because Herzigova was married to Bon Jovi drummer Tico Torres throughout the alleged affair.
18 of 23
The actor is credited with dating model-turned-actress Phillips in 1998 and jumpstarting the starlet's career, introducing her to Black and White director James Toback.
19 of 23
The actor's second fling of 1998 was with another model-turned-actress. As the story allegedly goes, man spots model in a magazine, man has his people call hers to arrange meet-up, man and model briefly date. Basically, DiCaprio makes dating look easier than flipping through a catalogue.
20 of 23
It's no secret the longtime pals have been praised for their onscreen chemistry — both in 1997's Titanic and 2008's Revolutionary Road — but unfortunately for fans, their offscreen relationship is strictly platonic. "The closeness and the strength of the friendship that we had is something a lot of my friends envy like mad," Winslet recalled of her time with DiCaprio on the set of Titanic. "But to me, he's just silly old Leo."
21 of 23
Titanic served as DiCaprio's ticket to all of Hollywood's glory, including the dating field. The actor allegedly chose Christensen as the first model to take out post-iceberg in 1998.
22 of 23
Zang snagged some time with DiCaprio before he transformed into a Titantic megastar. Not quite star-crossed lovers, this couple did attend the premiere of Romeo + Juliet together.
23 of 23
Hall has the honor of being the first supermodel connected to the actor. The pair were spotted canoodling together in 1994, but never confirmed their relationship. Rumors abound that Hall ultimately found the experience "disappointing."
Robert Pattinson Meets Bella Hadid, Plus Nina Dobrev, Diane Kruger & Many More
All About Fentanyl, the Drug That Killed Prince and Tom Petty — and Is Sweeping the U.S.
From Kanye & Chance to Barack & Michelle: Celebrities Who Hail from Chicago
14 Times Chrissy Teigen Was Almost Too Hot for Instagram
Star Tracks: Celebs on Social